#------------------------------------------------------------------------------
#$Date: 2015-08-13 05:23:10 +0300 (Thu, 13 Aug 2015) $
#$Revision: 153396 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/10/2241009.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241009
loop_
_publ_author_name
'Ishikawa, Yoshinobu'
_publ_section_title
;
 Crystal structure of 6,7-dichloro-4-oxo-4H-chromene-3-carbaldehyde
;
_journal_coeditor_code           ZL2636
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o652
_journal_page_last               o653
_journal_paper_doi               10.1107/S2056989015014644
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H4 Cl2 O3'
_chemical_formula_moiety         'C10 H4 Cl2 O3'
_chemical_formula_sum            'C10 H4 Cl2 O3'
_chemical_formula_weight         243.05
_chemical_name_systematic
;
6,7-Dichloro-4-oxo-4H-chromene-3-carbaldehyde
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.72(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   3.7695(13)
_cell_length_b                   6.1465(16)
_cell_length_c                   39.431(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    140
_cell_measurement_theta_max      17.22
_cell_measurement_theta_min      15.22
_cell_volume                     913.5(5)
_computing_cell_refinement
;
WinAFC Diffractometer Control Software (Rigaku, 1999)
;
_computing_data_collection
;
WinAFC Diffractometer Control Software (Rigaku, 1999)
;
_computing_data_reduction
;
WinAFC Diffractometer Control Software (Rigaku, 1999)
;
_computing_molecular_graphics
;
CrystalStructure (Rigaku, 2015)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2011 (Burla et al.,  2012)
;
_diffrn_ambient_temperature      140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku AFC--7R'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            5075
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.825
_diffrn_reflns_theta_min         3.100
_diffrn_standards_decay_%        0.632
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North et al., 1968)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0487P)²+0.5553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                1747
_reflns_number_total             2089
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            zl2636sup1.cif
_cod_data_source_block           I
_cod_database_code               2241009
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 0.55004(14) 0.47912(8) 0.27821(2) 0.02586(15) Uani d 1
Cl Cl2 0.92228(14) 0.92474(8) 0.29767(2) 0.02698(15) Uani d 1
O O1 0.8830(4) 0.6908(2) 0.41933(3) 0.0230(3) Uani d 1
O O2 0.3678(4) 0.1171(2) 0.40111(3) 0.0274(3) Uani d 1
O O3 0.7039(5) 0.2474(3) 0.49732(4) 0.0373(4) Uani d 1
C C1 0.8118(6) 0.5474(3) 0.44408(5) 0.0224(4) Uani d 1
H H1 0.8796 0.5864 0.4666 0.027 Uiso calc 1
C C2 0.6523(5) 0.3530(3) 0.43968(4) 0.0208(4) Uani d 1
C C3 0.5328(5) 0.2856(3) 0.40621(5) 0.0199(4) Uani d 1
C C4 0.5555(5) 0.3935(3) 0.34486(4) 0.0192(4) Uani d 1
H H2 0.4430 0.2604 0.3389 0.023 Uiso calc 1
C C5 0.6442(5) 0.5401(3) 0.31980(5) 0.0197(4) Uani d 1
C C6 0.8083(5) 0.7381(3) 0.32843(4) 0.0189(4) Uani d 1
C C7 0.8846(5) 0.7862(3) 0.36175(5) 0.0199(4) Uani d 1
H H3 0.9962 0.9196 0.3678 0.024 Uiso calc 1
C C8 0.6295(5) 0.4389(3) 0.37891(4) 0.0180(4) Uani d 1
C C9 0.7948(5) 0.6354(3) 0.38648(4) 0.0188(4) Uani d 1
C C10 0.5952(6) 0.2085(3) 0.46908(5) 0.0278(5) Uani d 1
H H4 0.4657 0.0777 0.4655 0.033 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C9 118.23(15)
O1 C1 C2 125.47(16)
O1 C1 H1 117.3
C2 C1 H1 117.3
C1 C2 C3 120.25(17)
C1 C2 C10 120.05(17)
C3 C2 C10 119.69(17)
O2 C3 C2 122.92(17)
O2 C3 C8 123.27(16)
C2 C3 C8 113.81(16)
C5 C4 C8 120.70(17)
C5 C4 H2 119.7
C8 C4 H2 119.7
C4 C5 C6 120.10(16)
C4 C5 Cl1 119.51(14)
C6 C5 Cl1 120.40(15)
C7 C6 C5 120.28(17)
C7 C6 Cl2 118.54(15)
C5 C6 Cl2 121.18(14)
C6 C7 C9 118.52(17)
C6 C7 H3 120.7
C9 C7 H3 120.7
C9 C8 C4 117.65(17)
C9 C8 C3 120.72(16)
C4 C8 C3 121.63(16)
O1 C9 C8 121.32(16)
O1 C9 C7 115.91(16)
C8 C9 C7 122.76(16)
O3 C10 C2 123.64(19)
O3 C10 H4 118.2
C2 C10 H4 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7148(19)
Cl2 C6 1.7275(19)
O1 C1 1.344(2)
O1 C9 1.376(2)
O2 C3 1.223(2)
O3 C10 1.206(2)
C1 C2 1.348(3)
C1 H1 0.9500
C2 C3 1.450(2)
C2 C10 1.478(3)
C3 C8 1.480(3)
C4 C5 1.381(3)
C4 C8 1.396(2)
C4 H2 0.9500
C5 C6 1.405(3)
C6 C7 1.374(2)
C7 C9 1.391(3)
C7 H3 0.9500
C8 C9 1.390(3)
C10 H4 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 O3 3_766 0.95 2.341 3.187(3) 148.01(13) yes
C7 H3 O2 1_665 0.95 2.263 3.129(2) 151.30(12) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 O1 C1 C2 -1.5(3)
O1 C1 C2 C3 -1.7(3)
O1 C1 C2 C10 178.9(2)
C1 C2 C3 O2 -175.48(19)
C10 C2 C3 O2 3.9(3)
C1 C2 C3 C8 4.7(3)
C10 C2 C3 C8 -175.96(18)
C8 C4 C5 C6 -0.5(3)
C8 C4 C5 Cl1 179.93(15)
C4 C5 C6 C7 0.6(3)
Cl1 C5 C6 C7 -179.76(15)
C4 C5 C6 Cl2 -179.99(15)
Cl1 C5 C6 Cl2 -0.4(2)
C5 C6 C7 C9 -0.2(3)
Cl2 C6 C7 C9 -179.59(15)
C5 C4 C8 C9 -0.1(3)
C5 C4 C8 C3 179.21(18)
O2 C3 C8 C9 175.37(19)
C2 C3 C8 C9 -4.8(3)
O2 C3 C8 C4 -3.9(3)
C2 C3 C8 C4 175.93(17)
C1 O1 C9 C8 1.4(3)
C1 O1 C9 C7 -177.98(17)
C4 C8 C9 O1 -178.76(17)
C3 C8 C9 O1 1.9(3)
C4 C8 C9 C7 0.6(3)
C3 C8 C9 C7 -178.76(18)
C6 C7 C9 O1 178.95(17)
C6 C7 C9 C8 -0.4(3)
C1 C2 C10 O3 -4.9(4)
C3 C2 C10 O3 175.8(2)

_cod_database_fobs_code 2241009
